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- W765709407 abstract "This thesis has been divided into three main sections. The first chapter contains areview of calixarene chemistry, in particular that relating to calix[4)resorcinarenes.Results and discussion are compiled in chapters two through seven and experimentaldetails are provided in chapter eight.Chapters two and three contain results and discussion relating to the novel synthesisof the first example of an enantiomerically pure axially chiral resorcinarene derivative.Chapter two outlines the key step in the reaction sequence, that being thetetramethylation of diastereomerically pure tetrakis(3,4-dihydro-2H-1,3-benzoxazine)calix[4)resorcinarene derivatives. Chapter three describes thesubsequent synthetic sequence developed to fragment 3,4-dihydro-2H-1,3-benzoxazines with a view to removing the a-methylbenzylamine chiral auxiliary, whichwas used to set up the observed axial chirality of the resorcinarene. The sequenceincorporates a novel modified Eschweiler-Clarke reaction whereby refluxing therequired tetrakis(3,4-dihydro-2H-1 ,3-benzoxazine)calix[4)resorcinarene derivative inaqueous formic acid resulted in reductive ring opening, furnishing the N-methylatedanalogue.Chapter four describes work on functionalising the 'lower rim' of resorcinarenemacrocycles with a view to forming derivatives with a pendant functional group thatcould be manipulated further to support the newly formed axially chiral resorcinarenederivatives onto solid supports.Chapter five contains prelfminary investigations into the use of axially chiralresorcinarene derivatives as chiral ligands in the enantioselective addition ofdiethylzinc to benzaldehyde.Chapter six contains results of investigations into the mechanism of the 'RetroMannich'reaction, whereby an amine exchange reaction is observed when refluxing adihydro-1,3-benzoxazine or Mannich base in a high boiling amine such asmorpholine. Evidence has been provided that the reaction proceeds via an o-quinonemethide intermediate.Chapter seven describes investigations into the generality of the modified EschweilerClarkereductive ring opening methodology whereby refluxing a formic acid solution ofa cyclic aminol ether results in the formation of N,N-dialkyl derivatives via reductivering opening. It was found that the procedure was general for compounds withoutsUbstituents at the two position. A second reaction protocol was developed forcompounds with substituents at the two position, utilising a combination of sodiumcyanoborohydride and chlorotrimethylsilane in acetonitrile to furnish the desired N,Ndialkylderivatives in excellent yield.Finally, chapter eight contains full experimental details for the synthetic studiescarried out in the preceding chapters." @default.
- W765709407 created "2016-06-24" @default.
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- W765709407 date "2001-01-01" @default.
- W765709407 modified "2023-09-23" @default.
- W765709407 title "Some aspects of the chemistry of cyclic aminol ethers" @default.
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